JP5913016B2 - ポリマー及び該ポリマーを含んだ有機発光素子 - Google Patents
ポリマー及び該ポリマーを含んだ有機発光素子 Download PDFInfo
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- JP5913016B2 JP5913016B2 JP2012198583A JP2012198583A JP5913016B2 JP 5913016 B2 JP5913016 B2 JP 5913016B2 JP 2012198583 A JP2012198583 A JP 2012198583A JP 2012198583 A JP2012198583 A JP 2012198583A JP 5913016 B2 JP5913016 B2 JP 5913016B2
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- 229920000642 polymer Polymers 0.000 title claims description 131
- 239000010410 layer Substances 0.000 claims description 124
- -1 2-ethylhexyl group Chemical group 0.000 claims description 93
- 239000000126 substance Substances 0.000 claims description 63
- 238000000034 method Methods 0.000 claims description 46
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 40
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 40
- 125000004431 deuterium atom Chemical group 0.000 claims description 37
- 229910052805 deuterium Inorganic materials 0.000 claims description 36
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 34
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 32
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 28
- 239000002019 doping agent Substances 0.000 claims description 22
- 125000005647 linker group Chemical group 0.000 claims description 21
- 125000003118 aryl group Chemical group 0.000 claims description 20
- 125000005843 halogen group Chemical group 0.000 claims description 20
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims description 20
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 19
- 125000001072 heteroaryl group Chemical group 0.000 claims description 19
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 19
- 125000006743 (C1-C60) alkyl group Chemical group 0.000 claims description 18
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 18
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 18
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 18
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 18
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 18
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 18
- 125000006749 (C6-C60) aryl group Chemical group 0.000 claims description 17
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 17
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 17
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 17
- 125000006745 (C2-C60) alkynyl group Chemical group 0.000 claims description 15
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 15
- 239000000758 substrate Substances 0.000 claims description 15
- 125000006818 (C3-C60) cycloalkyl group Chemical group 0.000 claims description 14
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 14
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 14
- 125000006746 (C1-C60) alkoxy group Chemical group 0.000 claims description 13
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims description 13
- 125000006744 (C2-C60) alkenyl group Chemical group 0.000 claims description 12
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims description 12
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 12
- 125000006751 (C6-C60) aryloxy group Chemical group 0.000 claims description 11
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 11
- 125000004115 pentoxy group Chemical group [*]OC([H])([H])C([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims description 10
- 125000006752 (C6-C60) arylthio group Chemical group 0.000 claims description 9
- 229910052757 nitrogen Inorganic materials 0.000 claims description 9
- 125000006612 decyloxy group Chemical group 0.000 claims description 8
- 125000005446 heptyloxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 claims description 8
- 125000003707 hexyloxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 claims description 8
- 125000006611 nonyloxy group Chemical group 0.000 claims description 8
- 125000005447 octyloxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 claims description 8
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 7
- 239000012044 organic layer Substances 0.000 claims description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
- 229910052799 carbon Inorganic materials 0.000 claims description 6
- 229910052741 iridium Inorganic materials 0.000 claims description 6
- 229920005603 alternating copolymer Polymers 0.000 claims description 5
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 5
- 125000001624 naphthyl group Chemical group 0.000 claims description 4
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- 229910052762 osmium Inorganic materials 0.000 claims description 2
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- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 6
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- 125000000008 (C1-C10) alkyl group Chemical group 0.000 description 4
- 125000006736 (C6-C20) aryl group Chemical group 0.000 description 4
- 125000003860 C1-C20 alkoxy group Chemical group 0.000 description 4
- CUJRVFIICFDLGR-UHFFFAOYSA-N acetylacetonate Chemical compound CC(=O)[CH-]C(C)=O CUJRVFIICFDLGR-UHFFFAOYSA-N 0.000 description 4
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- POILWHVDKZOXJZ-ARJAWSKDSA-M (z)-4-oxopent-2-en-2-olate Chemical compound C\C([O-])=C\C(C)=O POILWHVDKZOXJZ-ARJAWSKDSA-M 0.000 description 3
- VQGHOUODWALEFC-UHFFFAOYSA-N 2-phenylpyridine Chemical compound C1=CC=CC=C1C1=CC=CC=N1 VQGHOUODWALEFC-UHFFFAOYSA-N 0.000 description 3
- 229910000838 Al alloy Inorganic materials 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000007983 Tris buffer Substances 0.000 description 3
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 3
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 3
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- XKBGEWXEAPTVCK-UHFFFAOYSA-M methyltrioctylammonium chloride Chemical compound [Cl-].CCCCCCCC[N+](C)(CCCCCCCC)CCCCCCCC XKBGEWXEAPTVCK-UHFFFAOYSA-M 0.000 description 3
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- IYZMXHQDXZKNCY-UHFFFAOYSA-N 1-n,1-n-diphenyl-4-n,4-n-bis[4-(n-phenylanilino)phenyl]benzene-1,4-diamine Chemical compound C1=CC=CC=C1N(C=1C=CC(=CC=1)N(C=1C=CC(=CC=1)N(C=1C=CC=CC=1)C=1C=CC=CC=1)C=1C=CC(=CC=1)N(C=1C=CC=CC=1)C=1C=CC=CC=1)C1=CC=CC=C1 IYZMXHQDXZKNCY-UHFFFAOYSA-N 0.000 description 2
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- 239000011734 sodium Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- 229910052712 strontium Inorganic materials 0.000 description 1
- CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical compound [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 229940042055 systemic antimycotics triazole derivative Drugs 0.000 description 1
- GZCRRIHWUXGPOV-UHFFFAOYSA-N terbium atom Chemical compound [Tb] GZCRRIHWUXGPOV-UHFFFAOYSA-N 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 1
- 229910001887 tin oxide Inorganic materials 0.000 description 1
- 238000002834 transmittance Methods 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- WLPUWLXVBWGYMZ-UHFFFAOYSA-N tricyclohexylphosphine Chemical compound C1CCCCC1P(C1CCCCC1)C1CCCCC1 WLPUWLXVBWGYMZ-UHFFFAOYSA-N 0.000 description 1
- 125000003960 triphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C3=CC=CC=C3C12)* 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 229910052724 xenon Inorganic materials 0.000 description 1
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 1
- NAWDYIZEMPQZHO-UHFFFAOYSA-N ytterbium Chemical compound [Yb] NAWDYIZEMPQZHO-UHFFFAOYSA-N 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
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- H—ELECTRICITY
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
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- H10K85/10—Organic polymers or oligomers
- H10K85/111—Organic polymers or oligomers comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene
- H10K85/113—Heteroaromatic compounds comprising sulfur or selene, e.g. polythiophene
- H10K85/1135—Polyethylene dioxythiophene [PEDOT]; Derivatives thereof
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- C08G61/12—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule
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- C08G61/12—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule
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- C08G61/124—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides derived from five-membered heterocyclic compounds with a five-membered ring containing one nitrogen atom in the ring
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- H05B33/00—Electroluminescent light sources
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- H10K85/342—Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising iridium
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- C08G2261/31—Monomer units or repeat units incorporating structural elements in the main chain incorporating aromatic structural elements in the main chain
- C08G2261/312—Non-condensed aromatic systems, e.g. benzene
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- C08G2261/31—Monomer units or repeat units incorporating structural elements in the main chain incorporating aromatic structural elements in the main chain
- C08G2261/314—Condensed aromatic systems, e.g. perylene, anthracene or pyrene
- C08G2261/3142—Condensed aromatic systems, e.g. perylene, anthracene or pyrene fluorene-based, e.g. fluorene, indenofluorene, or spirobifluorene
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- C08G2261/30—Monomer units or repeat units incorporating structural elements in the main chain
- C08G2261/32—Monomer units or repeat units incorporating structural elements in the main chain incorporating heteroaromatic structural elements in the main chain
- C08G2261/324—Monomer units or repeat units incorporating structural elements in the main chain incorporating heteroaromatic structural elements in the main chain condensed
- C08G2261/3241—Monomer units or repeat units incorporating structural elements in the main chain incorporating heteroaromatic structural elements in the main chain condensed containing one or more nitrogen atoms as the only heteroatom, e.g. carbazole
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- C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G2261/90—Applications
- C08G2261/95—Use in organic luminescent diodes
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
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- H10K2101/10—Triplet emission
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
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- Polymers & Plastics (AREA)
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- Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Crystallography & Structural Chemistry (AREA)
- Inorganic Chemistry (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Electroluminescent Light Sources (AREA)
- Polyoxymethylene Polymers And Polymers With Carbon-To-Carbon Bonds (AREA)
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KR1020110092224A KR101830784B1 (ko) | 2011-09-09 | 2011-09-09 | 폴리머 및 상기 폴리머를 포함한 유기 발광 소자 |
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EP (1) | EP2568774B1 (ko) |
JP (1) | JP5913016B2 (ko) |
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US10636978B2 (en) * | 2014-12-30 | 2020-04-28 | Universal Display Corporation | Organic electroluminescent materials and devices |
JP2019501537A (ja) * | 2015-11-10 | 2019-01-17 | ノヴァレッド ゲーエムベーハー | 金属含有層の製造方法 |
US20190157599A1 (en) * | 2016-01-08 | 2019-05-23 | Konica Minolta, Inc. | Thin film and organic electroluminescent element |
CN109608625B (zh) * | 2018-11-16 | 2020-06-26 | 中国科学技术大学 | 有机共轭聚合物荧光材料及其合成方法 |
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WO2002026856A1 (en) * | 2000-09-26 | 2002-04-04 | Cambridge Display Technology Limited | Twisted polymers, uses thereof and processes for the preparation of statistical copolymers |
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US6984461B2 (en) * | 2002-06-21 | 2006-01-10 | Samsung Sdi Co., Ltd. | Blue electroluminescent polymer and organic-electroluminescent device using the same |
US20040202892A1 (en) * | 2003-04-08 | 2004-10-14 | Jsr Corporation | Polymer, polymer for forming organic electroluminescence device, polymer composition for organic electroluminescence device and organic electroluminescence device |
ITRM20040403A1 (it) | 2004-08-05 | 2004-11-05 | Pasteur Institut | Mutanti di shigella nelle funzioni relative ai processi di maturazione e riciclaggio dei peptidoglicani e loro usi come immunogeni. |
KR100762832B1 (ko) * | 2004-12-03 | 2007-10-02 | 주식회사 엘지화학 | 광반응성 화합물, 이를 이용한 액정 배향막, 그 제조방법및 상기 배향막을 포함하는 액정표시소자 |
TW200639193A (en) | 2004-12-18 | 2006-11-16 | Merck Patent Gmbh | Electroluminescent polymers and their use |
KR101328972B1 (ko) * | 2006-01-26 | 2013-11-13 | 삼성디스플레이 주식회사 | 전계발광 고분자 및 이를 이용한 유기 전계발광 소자 |
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JP5298460B2 (ja) | 2006-06-08 | 2013-09-25 | コニカミノルタ株式会社 | 有機エレクトロルミネッセンス素子、表示装置および照明装置 |
US7906274B2 (en) | 2007-11-21 | 2011-03-15 | Molecular Imprints, Inc. | Method of creating a template employing a lift-off process |
TWI385235B (zh) | 2008-07-22 | 2013-02-11 | Ind Tech Res Inst | 有機化合物及包含其之有機電激發光裝置 |
KR20100048210A (ko) * | 2008-10-30 | 2010-05-11 | 다우어드밴스드디스플레이머티리얼 유한회사 | 신규한 유기 발광 화합물 및 이를 포함하는 유기 발광 소자 |
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WO2011002927A2 (en) * | 2009-06-30 | 2011-01-06 | Plextronics, Inc. | Novel compositions, methods and polymers |
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KR20130028577A (ko) | 2013-03-19 |
JP2013060595A (ja) | 2013-04-04 |
US9346912B2 (en) | 2016-05-24 |
CN102993412A (zh) | 2013-03-27 |
EP2568774B1 (en) | 2019-02-27 |
US20130240843A1 (en) | 2013-09-19 |
KR101830784B1 (ko) | 2018-02-22 |
CN102993412B (zh) | 2016-12-21 |
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